(9S,12S,15S)-1-(9H-fluoren-9-yl)-9,15-diisobutyl-12-methyl-3,7,10,13-tetraoxo-2-oxa-4,8,11,14-tetraazahexadecan-16-oic acid -Drug Synthesis Database

【结构式】

【分子编号】49366

【品名】(9S,12S,15S)-1-(9H-fluoren-9-yl)-9,15-diisobutyl-12-methyl-3,7,10,13-tetraoxo-2-oxa-4,8,11,14-tetraazahexadecan-16-oic acid

【CA登记号】

【分子式】C₃₃H₄₄N₄O₇

【分子量】608.73512

【元素组成】C 65.11% H 7.29% N 9.2% O 18.4%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(I)

The condensation of doxorubicin (I) with Fmoc-beta-alanyl-L-leucyl-L-alanyl-L-leucine (II) by means of HATU and DIEA in DMF gives the protected adduct (III), which is treated with piperidine in DMF to yield the deprotected adduct (IV). Finally, this compound is condensed with succinic anhydride (V) in the same solvent and treated with NaOH or NaHCO3 to afford the target sodium salt.

参考文献中间体

合成目标

【1】 Fernandez, A.-M.; et al.; N-Succinyl-(beta-alanyl-L-leucyl-L-alanyl-L-leucyl)doxorubicin: An extracellularly tumor-activated prodrug devoid of intravenous acute toxicity. J Med Chem 2001, 44, 22, 3750.
【2】 Lobl, T.J.; Trouet, A.; Fernandez, A.-M.; Nieder, M.H.; Yarranton, G.T.; Gangwar, S.; Viski, P.; Lewis, E.; Dubois, V. (Beckman Coulter, Inc.); Prodrug cpds. and process for preparation thereof. WO 0033888 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	49366	(9S,12S,15S)-1-(9H-fluoren-9-yl)-9,15-diisobutyl-12-methyl-3,7,10,13-tetraoxo-2-oxa-4,8,11,14-tetraazahexadecan-16-oic acid		C₃₃H₄₄N₄O₇	详情	详情
(II)	11675	(8S,10S)-10-[[(2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-8-glycoloyl-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione		C₂₇H₂₉NO₁₁	详情	详情
(III)	49367	9H-fluoren-9-ylmethyl 3-([(1S)-1-[([(1S)-2-[((1S)-1-[[((2S,3S,4S,6R)-6-[[(1S,3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-hydroxy-2-methyltetrahydro-2H-pyran-4-yl)amino]carbonyl]-3-methylbutyl)amino]-1-methyl-2-oxoethyl]amino)carbonyl]-3-methylbutyl]amino)-3-oxopropylcarbamate		C₆₀H₇₁N₅O₁₇	详情	详情
(IV)	49368	(2S)-2-[(3-aminopropanoyl)amino]-N-[(1S)-2-[((1S)-1-[[((2S,3S,4S,6R)-6-[[(1S,3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-hydroxy-2-methyltetrahydro-2H-pyran-4-yl)amino]carbonyl]-3-methylbutyl)amino]-1-methyl-2-oxoethyl]-4-methylpentanamide		C₄₅H₆₁N₅O₁₅	详情	详情
(V)	11291	Dihydro-2,5-furandione; Succinic anhydride	108-30-5	C₄H₄O₃	详情	详情

Extended Information